I've paddled the length and breadth of the Chesapeake for days on end, the ocean coasts of Maryland and Virginia too. But sometimes all one wants is an easy day trip, no worries about wind or tide, just a few hours to meander by canoe or kayak.

The uppermost five or six miles of the Chester River, between the Maryland Eastern Shore villages of Crumpton and Millington, filled the bill dandily on a recent morning. "A pastoral scene of rich bottom lands, patches of intensely green woods, an occasional village," Hulbert Footner described the Chester region of Kent and Queen Anne's counties 70 years ago in his classic, "Rivers of the Eastern Shore."

One still could. Even the ride east to our launch site across heavily traversed U.S. Route 301 was strikingly bucolic once we left the environs of Kent Island at the Chester's miles-wide mouth. Footner lavished many a word on the Chester and its picturesque old Kent county seat of Chestertown; but of the river above Crumpton he had only this: "there the steamboats turned around and went back."

Most power boats still do—extensive shallows and unmarked channels on up to Millington, the head of tide and near the head of navigation — even for kayaks — make this stretch of water a paddlers' dream.

Crumpton's public boat ramp, just off Front Street, offers an all too rare example of an ideal put-in for paddle craft — a flat, sandy little beach adjacent to the typical roughened concrete ramp that is perfect for boat trailers, but chews up hulls of canoes and kayaks.

We chose to head upstream with the tide, but tide this far upriver is fairly weak. Wind is the route-decider — if it is more than 12–15 mph, most won't like going against it.

For a short stretch of water, the Chester changes its nature frequently. It's still broad water by Crumpton, half a mile or so, but serene today and reflective of puffy clouds and a blue sky. Ospreys surveil our progress as they fish. The banks, as Crumpton falls behind, are high and mostly forested, gorgeously arrayed.

The long, cool spring has coaxed the vegetation to peak performance. Two hawks, a red-tailed and a red-shouldered, soar over us.

The upper Chester is excellent spawning ground for many Bay species all the way to Millington. In April, said Tyler Campbell, a local photographer and river activist paddling with us, fishermen thronged here to cast for yellow perch, one of the estuary's most colorful and tastiest species. Thanks to conservation efforts by both sport and commercial fishermen, the runs of both yellow and the more abundant white perch appear fairly healthy here.

A couple miles above Crumpton, the Chester narrows and winds sinuously between freshwater marshes and forests of oak, tulip poplar, sweet gum and pines.

It is still a mystery why rivers and streams seldom run in a straight line for long unless ditched and channelized by humans, said Karl Kehm, a physics professor from Washington College in Chestertown, MD, who is also paddling with us.

"Even Einstein wondered about why this is, and wrote about it, but neither he nor anyone has totally figured it out," Kehm said. We talk about how a straight line may be the fastest way to get from point A to point B — but surely not the best way — as we watch a flock of yellowlegs, shorebirds that migrate all the way from Argentina, wheeling over one of the meandering marshes.

If one wishes to make an even shorter paddle of the upper Chester, there's an option halfway up to Millington at Shading Reach, an old summer campground community with a little launch ramp and road access from Route 291. It would be short work to stash a bicycle here, launch at Crumpton or Millington, then pedal back to the car. I often avoid the need for two vehicles this way on paddles.

Over sandwiches at Shading Reach at a sunny picnic table by the river—now becoming a stream—I asked Campbell how the Chester's doing environmentally. He's a charter member of the Chester River Association, begun 28 years ago to advocate for the river's health.

One of Campbell's specialties is taking photographs as he flies his airplane. The water we're paddling through today would look a lot browner, more turbid, gazing straight down from aloft, he said. Like the Chesapeake as a whole, the river has too much sediment and too many nutrients like nitrogen and phosphorus.

The Chester River Association has about 50 trained volunteer testers who monitor water quality year-round from top to bottom. Report cards the CRA issues have shown mostly Ds and Cs since 2007; most recently the river as a whole scored "about a C," Campbell said.

A lot of the association's work involves teaming with farmers to reduce polluted runoff. Agriculture encompasses nearly two thirds of the river's 250,000-acre watershed, which extends from the Chesapeake into Kent and Newcastle counties in Delaware.

From his overflights, "it seems farmers are doing the right things," Campbell said. I thought about this later as I drove away from the upper Chester on a road bordered for half a mile or so by huge, plowed fields; wondered whether we're just doing things now on such a huge scale, both in agriculture and development, that it just overwhelms water quality efforts.

But today's not the day to dwell on such weighty thoughts. The Chester just gets nicer and nicer above Shading Reach, with little coves and oxbows opening to either side of the main stream, inviting those who want to enter and poke around, drift, birdwatch, eat an apple or lean back and watch an eagle against the sky.

A caution: As you draw within sound, and almost within sight of U.S. 301, keep to the left and use a GPS if you've got one, or an app on the cell phone. The river crosses under the dual highway in two places, but only the leftmost will go to Millington. It might be the prettiest passage under a major U.S. highway in these parts, canopied by sycamore and river birch, dogwoods poking from the understory.

Before you know it you have reached the pullout, Millington's little riverfront park, on the right just before the Route 313 bridge. It's a one-boat-at-a time, steepish, dirt track, not so easy as the put-in at Crumpton. We actually pulled out just past the bridge on a grassy bank, and carried our kayaks across 313 to the cars in the little park.

"What do you catch?" I asked Lewis Legg, an old fisherman and resident here all his life who was casting into the barely 100-foot wide Chester there. "Yellow perch, white perch, shad, herring, rockfish — right now only allowed to keep white perch," he said. Indeed, shad and herring are under moratoria; rockfish and yellow perch are out of season.

None of that much applied when Legg was younger. He and his grandfather used to gill-net spawning shad from Millington down to Shading (pronounced shadding) Reach, he said. Their roe — rolled in cornmeal and fried by his grandmother— is among his fond memories.

On your own on the Upper Chester

Paddling the upper Chester is largely a do-it-yourself experience. Chester River Kayak Adventures runs paddling trips, but largely on the lower river. The Sultana Project in Chestertown, a nonprofit education group, periodically takes Saturday groups paddling in these parts. Chester River Outfitters in Chestertown rents kayaks.

And for another day paddle view of the upper Chester, Chris Cerino of the Sultana Project highly recommends launching on Morgan Creek at a small public landing at the end of Riley's Mill Road about 4 miles north of Chestertown off of Route 213. He likes the autumn there: "great foliage, lots of eagles, ospreys, red-tailed hawks, herons…lot of waterfowl…bald eagle nest in a big sycamore tree within view of the landing…about three miles round trip from launch to head of navigation…high tide recommended."

Tom Horton

Tom Horton has written about Chesapeake Bay for more than 40 years, including eight books. He lives in Salisbury, where he is also a professor of Environmental Studies at Salisbury University.

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